GB833474A - Piperazine derivatives - Google Patents
Piperazine derivativesInfo
- Publication number
- GB833474A GB833474A GB38774/57A GB3877457A GB833474A GB 833474 A GB833474 A GB 833474A GB 38774/57 A GB38774/57 A GB 38774/57A GB 3877457 A GB3877457 A GB 3877457A GB 833474 A GB833474 A GB 833474A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperazine
- give
- propyl
- phenothiazyl
- hydroxyethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- -1 ester radical Chemical class 0.000 abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 3
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- BZEJZIAESDBOJX-UHFFFAOYSA-N 10-(3-chloropropyl)-2-(trifluoromethyl)phenothiazine Chemical compound C1=CC=C2N(CCCCl)C3=CC(C(F)(F)F)=CC=C3SC2=C1 BZEJZIAESDBOJX-UHFFFAOYSA-N 0.000 abstract 1
- RKGYJVASTMCSHZ-UHFFFAOYSA-N 2-(trifluoromethyl)-10H-phenothiazine Chemical compound C1=CC=C2NC3=CC(C(F)(F)F)=CC=C3SC2=C1 RKGYJVASTMCSHZ-UHFFFAOYSA-N 0.000 abstract 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 abstract 1
- LWEOFVINMVZGAS-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-ol Chemical compound OCCCN1CCNCC1 LWEOFVINMVZGAS-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 abstract 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 abstract 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical class CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0833474/IV (b)/1> and their pharmaceutically acceptable acid addition salts, and the preparation thereof by condensing a compound of the general formula <FORM:0833474/IV (b)/2> with a piperazine of the formula <FORM:0833474/IV (b)/3> wherein n is 1 or 2, R1 is a hydrogen atom or a lower alkyl group or the residue of a lower aliphatic carboxylic acid (the term "lower" indicating not more than 6 carbon atoms in the group so described) and of P and Q one is hydrogen and the other is a group CH2CH2CH2X or CH2CH2COX, X being a reactive electronegative atom or radical, such as a p halogen atom or an aryl sulphonic ester radical, and if necessary reducing CH2CH2CO to propylene. The reaction is preferably carried out in the presence of a basic condensing agent. In an example, 2-trifluoromethylphenothiazine is condensed with 1-chloro-3-bromopropane in the presence of sodium amide and liquid ammonia, to form 10-(3-chloropropyl)-2-trifluoromethylphenothiazine which is heated with 1-(2hydroxyethyl)-piperazine to give 1-(2-hydroxyethyl) - 4 - [3 - (2 - trifluoromethyl - 10 - phenothiazyl)-propyl]-piperazine. Similarly, but using 1 - (3 - hydroxypropyl) - piperazine the corresponding propyl analogue is obtained. In further examples the 1-(2-hydroxyethyl) derivative is reacted with phenyl chlorocarbonate to give the corresponding phenyl carbonate ester and this in turn with ammonia yields the carbamate of 1-(2-hydroxyethyl)-4-[3-(2trifluoromethyl - 10 - phenothiazyl) - propyl]piperazine; with dimethylcarbamyl chloride to give the dimethylcarbamate ester; with ethyl chlorocarbonate to give the ethyl carbonate ester (both with the 1-(2-hydroxy)ethyl) and 1-(3-hydroxypropyl) derivatives); and with acetic or propionic anhydrides to give the acetate or propionate esters. Condensing 10gives 1 - (2 - ethoxyethyl) - 4 - [3 - 2 - trifluoromethyl - 10 - phenothiazyl) - propyl] - piperazine. The dihydrochlorides and dimaleates of the esters above are also described.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US356775XA | 1956-12-13 | 1956-12-13 | |
| CH349268T | 1957-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB833474A true GB833474A (en) | 1960-04-27 |
Family
ID=25737052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB38774/57A Expired GB833474A (en) | 1956-12-13 | 1957-12-13 | Piperazine derivatives |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH356775A (en) |
| DE (1) | DE1168434B (en) |
| GB (1) | GB833474A (en) |
| MY (1) | MY6200102A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3169962A (en) * | 1963-02-28 | 1965-02-16 | Olin Mathieson | Benzhydryl ethers of 10-(hydroxyethylpiperazinopropyl) phenothiazines |
| US3282934A (en) * | 1964-05-15 | 1966-11-01 | Schering Corp | Nitrogenous esters of hydroxylalkylamino phenothiazines |
| WO2013138101A2 (en) | 2012-03-16 | 2013-09-19 | Children's Medical Center Corporation | Calmodulin inhibitors for the treatment of ribosomal disorders and ribosomapathies |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2694705A (en) * | 1954-11-16 | Nx c c ox a a | ||
| GB666457A (en) * | 1948-10-30 | 1952-02-13 | Henri Morren | Carbonyl chlorides and monocarboxyamides of piperazine and process for the preparation thereof |
| BE558008A (en) * | 1956-06-21 |
-
1957
- 1957-12-09 CH CH356775D patent/CH356775A/en unknown
- 1957-12-12 DE DESCH23239A patent/DE1168434B/en active Pending
- 1957-12-13 GB GB38774/57A patent/GB833474A/en not_active Expired
-
1962
- 1962-12-31 MY MY1962102A patent/MY6200102A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3169962A (en) * | 1963-02-28 | 1965-02-16 | Olin Mathieson | Benzhydryl ethers of 10-(hydroxyethylpiperazinopropyl) phenothiazines |
| US3282934A (en) * | 1964-05-15 | 1966-11-01 | Schering Corp | Nitrogenous esters of hydroxylalkylamino phenothiazines |
| WO2013138101A2 (en) | 2012-03-16 | 2013-09-19 | Children's Medical Center Corporation | Calmodulin inhibitors for the treatment of ribosomal disorders and ribosomapathies |
| EP3461482A1 (en) | 2012-03-16 | 2019-04-03 | Children's Medical Center Corporation | Calcium channel blockers for the treatment of ribosomal disorders and ribosomapathies |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1168434B (en) | 1964-04-23 |
| MY6200102A (en) | 1962-12-31 |
| CH356775A (en) | 1961-09-15 |
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